Antiparasitic isoxazoline compounds, long-acting injectable formulations comprising them, methods and uses thereof

A technology of isoxazoline and compounds, applied in the field of isoxazoline compounds, can solve problems such as economic loss, impact on animal nutrition, impact on companion animals and poultry

Active Publication Date: 2018-12-21
BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These parasites adversely affect the nutrition of the animals and cause severe economic losses in pigs, sheep, horses and cattle, as well as affecting companion animals and poultry

Method used

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  • Antiparasitic isoxazoline compounds, long-acting injectable formulations comprising them, methods and uses thereof
  • Antiparasitic isoxazoline compounds, long-acting injectable formulations comprising them, methods and uses thereof
  • Antiparasitic isoxazoline compounds, long-acting injectable formulations comprising them, methods and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[1594] Preparation method of compound of formula (Id)

[1595] Approved from US 7964204, US 8410153, US 8546,618, US 8217180, US 8 546613, US7662972, US 8466115, US 8383659, US 8853186, US 8618126, US 2014 / 0371464, US 2015 / 0291612 and WO 2014 / 090918 ( They are all incorporated herein by reference in their entirety by methods improved from those described in), which can prepare the compound of formula (Id) and the intermediates used in the method for preparing the compound.

[1596] In one embodiment, the compound of the present invention can be prepared according to the general method shown in the following scheme 1, wherein Y, Q, X 1 And X 2 As defined above with respect to formula (Id), W is Cl, Br or I, and R is an alkyl group.

[1597] plan 1

[1598]

[1599] This general method is described in, for example, US 8,546,618 to prepare compounds where Y is Y-2. Using appropriately substituted compounds of formula Id-1 and Id-4, a variety of compounds of formula (Id) can be prepared...

Embodiment

[1898] The following non-limiting examples further describe the invention, which further illustrate the invention, and they are not intended and should not be construed as limiting the scope of the invention.

[1899] Synthesis Example

[1900] Synthesis Example 1: Synthesis of (S)-Ie

[1901] The compound of formula (S)-Ie of the present invention is prepared according to Scheme 2 below. Compound 2-1 is described in US 7,951,828 Bl (incorporated herein by reference). The preparation of compounds 2-4 is described in US 8,217,180 B2 and US 8,546,618 B2 (both of which are incorporated herein by reference in their entirety). According to operations described in, for example, US 9,126,995 B2, WO 2011 / 104089, and US2014 / 0206633 (all incorporated herein by reference), a cinchona alkaloid-based chiral phase transfer catalyst similar to 2-6 was prepared. In addition, Matoba et al., Angew. Chem. 2010, 122, 5898-5902 describe the use of these catalysts for the preparation of enantiomerical...

preparation Embodiment 5

[1928] Compound of formula (Ia) 30% (w / v)

[1929] Ethanol 9% (w / v)

[1930] PEG 400 QS.

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Abstract

This invention relates to long-acting injectable compositions for combating parasites in animals, comprising at least one isoxazoline active agent, a liquid PEG and / or a neutral oil, optionally a co-solvent, and optionally a pharmaceutically acceptable additive or excipient. This invention also provides new isoxazoline active agents with long-lasting efficacy against ectoparasites. The invention also provides for improved methods for eradicating, controlling, and preventing parasite infections and infestations in an animal comprising administering the novel isoxazoline compounds and long-acting injectable compositions of the invention to the animal in need thereof.

Description

Technical field [0001] The present invention provides insecticidal and antiparasitic isoxazoline compounds, and long-acting compounds comprising at least one isoxazoline active agent, liquid polyethylene glycol (PEG) and optionally a co-solvent Injectable composition. The present invention also provides the use of these compounds and compositions against pests and parasites (including ectoparasites (for example, fleas or ticks) and / or endoparasites), as well as for controlling pests and preventing Or methods to treat parasitic infections and infestations in animals. [0002] Cross references to related applications [0003] This application claims the benefits of U.S. Provisional Application No. 62 / 299,333 filed on February 24, 2016 and U.S. Provisional Application No. 62 / 379,348 filed on August 25, 2016, both of which are incorporated herein by reference. Background technique [0004] Animals (such as mammals and birds) are often susceptible to parasite infestation / infection. Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/80A61K47/00C07D261/04A01P7/04A01P7/02A01P3/00A61K9/00A61K31/422
CPCC07D261/04C07D413/04C07F5/025C07D491/107A01N43/80A01N43/90A01N55/08A61K31/69A61K31/42A61K31/422A61P33/14A61K9/10A61K9/08A61K9/107A61K9/0019A61K9/0095A61K47/10A61K47/14C07D471/04A61K31/415A01N25/02A01N25/22
Inventor L·P·勒希尔德法卢瓦C·Q·孟S·M·卡迪P·谢费茨I·加莱斯卡
Owner BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC
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